First Examples of Oxidizing Secondary Alcohols to Ketones in the Presence of the Disulfide Functional Group: Synthesis of Novel Diketone Disulfides.

The disulfide functionality is present in a number of organic compounds of interest in the fields of both chemistry and biology. Because the disulfide group is known to be highly susceptible to further oxidation by a wide range of agents, performing a chemoselective oxidation without further oxidizing the disulfide moiety poses a synthetic challenge. Reported herein are the first examples of such a chemoselective oxidation in which a series of novel secondary alcohol disulfides 2a−f have been converted to the corresponding symmetrical diketones 3a−f utilizing a modified Swern oxidation.